CHERISHED CHERYL

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Joseph, a traveling Bizarro author tells us his story of his master/slave relationship with the transgendered dominatrix, Cheryl.

In October of 2009, after my first summer of hitchhiking around the United States, I returned to Portland, Oregon and rented a cheap attic room of a house downtown. I began frequenting a dive bar called “Tony’s” a few blocks from my house and eventually started performing spoken word there for Thursday open mic nights. One week I went dressed in full drag and went sporting a beard. I read 3 pieces related to gender fucking. After the show, a woman named Cheryl came up to me and offered to buy me a drink. She was a poet , an international law student, she was incredibly smart and well read, very politically centered and had been living as a transgendered woman for 10 years.

We drank, we flirted, and we went back to my apartment and had sex. The first time we became physical, we only fooled around. I was still fairly inexperienced with male genitalia. I think what made it great the first time was that we didn’t hold back and weren’t worried about our performances, we simply had fun. We struck up a friendship and discovered we had quite a bit in common. I felt a connection and I was most definitely attracted to her from day one, but as for falling for her it was too early to tell. I feel there was a level of trust between us. She told me her birth name, the one she had before she began openly identifying as a female, which very few people in her life are privy to. I was a traveler and I knew I would be wandering again in the near future and I had been single for much of the last 4 years. I kept it in the back of my mind to not get heavily involved with anyone. Then one night she told me she had just been married to a man in Amsterdam that summer. She was going to go live with him when her studies were finished in Portland. She came forward with this information because she said she could see herself falling for me and she didn’t want to jeopardize her relationship with her husband. Then she hit me on the idea of being her submissive.
I had known her less than two weeks when she proposed the idea of a master/slave relationship. I had been in a Master/Slave relationship before, but the woman, who was my co-worker at the time, was inexperienced and not dominant enough, and more interested in just having sex with me. We were both first timers to the whole thing and it didn’t go so well. She was not the dominating type, and I quickly grew bored with it. We lasted all off a couple weeks. Cheryl was a different sort of girl (with a huge penis) and I thought it might work, so I consented to it.

We had a very simple agreement, we spoke beforehand about which days I was just her friend, and which ones I was her slave. During the time I was her slave, I had to follow her commands or I was punished.

After I became her slave, the dynamic changed, and necessarily so. I was made to beg her for sexual pleasure and I was usually denied it. Meanwhile she could ask me to do anything and I would comply. And I would do it immediately. There was the basic ”Do what I say, or I’ll harm you physically”, like getting my nipples bitten. I was forced to cook and clean for her, do her grocery shopping, and pleasure her whenever she desired.. Yes, I could have gotten up and walked out of her apartment at any time, but I wanted her to feel pleasured and I wanted to feel like I had no choice. I considered myself her slave most of the time. I would refer to her as “my Mistress” (and I still do) in conversation, and if she called me to come over, as long as I wasn’t working, I would do it. It can be hard for people to wrap their heads around that one because denying yourself freedom of choice seems contrary to our base desires.

In return for doing her every bidding, she worked on “feminizing” me. When I was acting as her slave, I was known only as “Lilly” and could only respond to that name. As Lilly, I was expected to act, both in mind and mannerisms, as a woman. I had to refer to myself in the feminine and would be punished for not doing so. She saw a woman inside of me and she wanted to bring it out. She taught me how to hold my body, my shoulders and back more femininely, and to keep my eyes open wide “cause the boys like that sort of thing.” From her I learned how to apply make-up, how to shave my body hair properly, and how to fix up my hair. She would take me out in public and humiliate me. Once she dolled me up in full makeup, a corset, ruffled miniskirt, thong, stockings, and high heels, and sent me on a walk to the store to buy her drinks. This was January, mind you. I froze my ass off and nearly killed myself trying to walk up and down Portland’s hilly streets in stilettos. I also practiced fellatio on her, she being preoperative, (as in she still had a penis) quite often. I found the act quite gratifying and I was a natural at it from the beginning. Deepthroat, which she wanted a lot, was a more difficult task. But it was a fun, challenging experience that I’m glad I put myself through: the art of making fun of gender differences, to be able to shock in a good way and to have someone that I find beautiful. That was new to me. It was immensely satisfying and the feeling was unique.

Unfortunately, the relationship was cut short unexpectedly by my having to return home, in the state of Idaho, to take care of a personal matter and sort the mess out. It ended very abruptly. I explained the situation and I think she took it as me trying to get out of the agreement. She kicked me out of her apartment. I tried contacting her by e-mail later in the year to find out how she was doing, but she never responded. We spoke a couple times after that, but never saw each other again.

I haven’t seen or heard from her since. I would have liked to keep some form of contact open. She was still going through the psychiatric evaluations required in the U.S. to be eligible for surgery when I knew her. She had been on hormones for years and it seemed that she would eventually be approved. I am curious to know if she has gotten to take that step toward becoming what she envisioned in her mind. If she hasn’t gotten to experience that yet, I hope she does soon. I would be excited to catch up, to tell her about my travels in Europe. I’d want to know if she had graduated college, if her marriage was working, and if she had given any thought to starting a family….

Experiencing another aspect of my gender, to see the world through a different lens was eye opening. I may have been the same person in most regards, but the world treated me differently when it thought I was a woman. I had men grab my ass in crowded public areas, something I didn’t realize was so common. I’ve always felt a little androgynous inside, have been attracted to males since I was kid, and started cross-dressing when I was nineteen. I kept these feelings and actions more on the private side until about a year before I met Cheryl. She helped open me up and I was very public about having an S&M relationship with an older, transgendered woman, much to my family’s chagrin. To change a man’s relationship with his identity isn’t necessarily the desired outcome for all men who submit to others, but it certainly can’t hurt. Well, actually, it hurts a lot, but the feeling your left with is a little bit of the bigger feeling that most woman and minorities have to live with their entire lives. As men, we’re already expected to be, and given plenty of opportunity, to be dominant. There aren’t so many men out there like me, willing to take the risk of damaging their pride or ego, to feel ashamed or humiliated. I don’t go around touting “My other penis is a vagina!” or anything like that, though. I don’t feel a sense of superiority for exploring gender roles, I just want to experience all that is available to me in life, all possibilities. I want to get inside the mind of a woman as much as I want to get inside the mind of an ant or a god.

I got something very important for me out of it, as well. I’ve always had a penchant for playing the rebel, balking at authority any chance I got, and this was a sort of therapy for me. It required me to suppress urges to fight back when I was forced to do things I normally wouldn’t. I feel like that stuck with me to a degree. I had always had a certain respect for order, but I think being forced to find acceptance in things I couldn’t control helped me learn to play better with other people in general, made it easier to deal with the bossy ones. Dominance and violence are not the only ways to bring about change, they just bring it much more quickly than other forms of behavior. Personally, I think education, both from experienced and learned individuals and through self-discovery, is the key to understanding our differences. It may seem contradictory to say, but the more differences I discover, the more closely related everything seems. When I begin relating, my universe gets a little bit smaller, a little bit more connected, and a whole lot more meaningful.